Dimethylformamide → Benzyl 4-(3-hydroxypropyl)piperidine-1-carboxylate

HRID 484485Notes

Reaction equation

HRID 484485 reaction equation
[BH4-].[Na+].CN(C)C=O.Cl[C:9](=[O:28])[CH2:10][CH2:11][CH:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[CH2:14][CH2:13]1>O>[OH:28][CH2:9][CH2:10][CH2:11][CH:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 4311764Sodium borohydrideHCID 12674069(Phenylmethyl) 4-(3-chloro-3-oxopropyl)-1-piperidinecarboxylate

Product 1

HCID 14989193Benzyl 4-(3-hydroxypropyl)piperidine-1-carboxylateYield 61.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred and cooled (ice bath, 10° C.) mixture of 3.4 parts of sodium tetrahydroborate and 188 parts of N,N-dimethylformamide were added dropwise 28 parts of (phenylmethyl) 4-(3-chloro-3-oxopropyl)-1-piperidinecarboxylate (exothermic reaction, the temperature rose to 38° C.). Upon completion addition, the reaction mixture was stirred over weekend at room temperature. The reaction mixture was poured into water and the product was extracted with methylbenzene. The extract was dried, filtered and evaporated, yielding 15.4 parts (61.6%) of (phenylmethyl) 4-(3-hydroxypropyl)-1-piperidinecarboxylate as a residue (int. 35).

Workup

  1. temperaturecooled
  2. customexothermic reaction
  3. customrose to 38° C.
  4. additionUpon completion addition
  5. stirringthe reaction mixture was stirred over weekend at room temperature
  6. extractionthe product was extracted with methylbenzene
  7. customThe extract was dried
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-e5fbd2d085b84ab38a8b8d7eecf78437
Source dataset
uspto-grants-1993_07
Patent number
US05231184

Reaction notes

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